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Final_keyc - Name First Z635 Last 3 L4(Q g 5 CWlD Seat...

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Unformatted text preview: Name: First Z635): Last 3 L4 )(Q g 5 CWlD: Seat Number: Chemistry 3053 Final Exam, 200 points Monday, December 12, 2011 GENERAL INSTRUCTIONS: 1) Write name, CWlD, and seat number on this page 2) Check for 14 pages (including this one and the last page with the periodic table). 3) Sign the attendance sheet when you turn in your exam. 4) Keep your exam flat on the desk in front of you. You may only have a writing utensil. EVERYTHING ELSE MUST BE PUT AWAY. No cell phones No calculators No electronic devices of any kind. Show Your Work. Be Specific With Your Answers and Write Legibly (if we can’t read it, we can’t grade it) GOOD LUCK When your exam is returned, your score will be on the last page. 1 Page Point Totael 1) Circle the arrow that indicates the direction of the following acid/base reactions. (9 points) b) ~. + ———————-—> é' Na // _ + CH3CH3 - + Na+CH20H3 C) H20 + HBr H30+ + B'" 2) Propose a reasonable mechanism for the following reaction. (5 points) / Q l, x H 8' M M) ( / \\,$ \__,,l 2 Page Point Totael \ t 3) Fill in the boxes with the major product formed from each reaction. (16 points) socrz H 80 M £1 HI MOH #9 MO 140C 1) TfCI, pyridine 2) CHBCHQO‘ 4) Show how the given product could be synthesize from the given starting material. a) (9 points) “41.th =Reagent 2. P H} = Reagent m : Product 3 Page Point Totael a5 b) (9 points) 0 / 2)“; CD“ = Reagent \ = Reagent 5g /‘\/‘\ = Product 9’ L/ ' \LMhbtt 5) Give the starting material that would afford the given product as the major product under the reaction conditions provided. (12 points) a) vat/Lav NaOH HOWOH Dr M5 L61 b) OH O H2CI'O4 \\ NaCN CN 4 Page Point Totael 94 6) Given the following information, give the structures for unknown compounds A, B, and C. (15 points) 1)CHImBnEto A = C10H1802 ——3—‘_2* B = CtOH2OO 2) H30+ UAm4 7) Mark the letter answer legibly (A, B, C, or D) for each question in the blank to the left. (20 points) 5 3) Identify which compound has the highest boiling point. A) B) o) D) o HO/\/\ HO/WOH /\O/\ \A/ C b) Identify the correct shape of ‘CMes. A) Tetrahedral B) linear C) trigonal pyramidal D) trigonal planar D 0) identify which Is the pKa for CH3CH3 (a very weak acid) i5 A) pKa- — 12 Arrpka— — —7 MpKa— — 35 @Ka— — 50 g 1 d) identify which compound is an electrophile. A) CH4 B) NH3 0) BCI3 o) 'OH 5 Page Point Totael I 2 e) Identify which compound is cis—1,3-dimethyl cyclopentane. A) CH3 B) CH3 0) CH3 D) CH3 Got (5 C) Q ”CH3 "’CHB CH3 A f) ldentify the structure that corresponds to 4-ethyl-3,5—dimethylcyclooctene A) B) C) D) I E; 9) Identify which anion would be the least nucleophilic in aprotic solvents. A) F' B) r C) Br‘ D) or Q h) Identify which alkyl halide would react the slowest via an 8N2 mechanism. D) A) B) F C) A i) For the following acid catalyzed dehydration reaction, identify the MAJOR product. /\(\OH H2804 heat D) A) B) C) “Y 6 A? W A j) For the following 2° carbocation, identify the most stable rearrangement product. CH3 3 H CH3 A) B) C) C D) + + + CH3 + + GACHS CH2 6 Page Point Totael 8) Fill in the blanks with the reagent(s) that would afford the given product as the major product. (15 points) 1) o o OJKOH 2) O/KH o q OH o” d) 61) Brow E0 7 Page Point Totael 9) Give the structure that corresponds to the following lUPAC name. (12 points) a) Ethyl phenyl ether b) (E)—But-2—en-1-ol c) Butane-1,2—4-triol Flo/\KVGA C5“ 10) Give the word that corresponds to the given definition: (9 points) a) The molecule or ion that forms when a base accepts a proton: l [313; l 5 “OJ: Odd b) The addition of water to an alkene to form an alcohol: WM 0) An equimolar mixture of enantiomers: [ “(fimjc mt‘fl’rwfi or" (“acmoirfl 8 Page Point Totael Q~l 11) a) Give the products of the following reaction: (6 points) b) Identify the isomeric relationship of the products from part a: (2 points) W3 0) For any chiral centers in the compounds from part a, CLEARLY designate R and/or S stereochemistry: (8 points) A=5 CaQ 15:2 0:5 d) Convert your products from part a into the Newman projections with the lowest energy staggered conformation, looking down bond C3-C4. (6 points) ”3:: 9 Page Point Totael 12) Give a Grignard Reagent and a carbonyl that could prepare the given alcohol? (12 points) )Grignard Reagent carbonyl - . Grignard Reagent carbonyl wb M335” “—“9 W H30 OH 13) a) Explain why the following reaction does not give the indicated product. (6 points) New»: Wt 0L 9W“ { <5m‘b “W reward—V b) What could be done or changed to synthesize the desired product. (5 points) puma umnt 10 Page Point Totael 14) a) Draw a chair conformation of Cis-l,3—dimethylcyclohexane and its ring flipped conformational isomer. (4 points) U‘s 0"} ugh/mg . ~————-———:=~ b) Draw a chair conformation of trans—1,3-dimethylcyclohexane and its ring flipped conformational isomer. (4 points) 0‘3 0) Which compound is expected to be more stable: cis-1,3—dimethylcyclohexane or trans—1,3— dimethylcyclohexane. Explain your reasoning. (4 points) 03 M be 6*ka becawfl’ LA: hour) ex mm ”51% no W W Coma/Q Sb no \2. (13.054le MGM‘W 11 Page Point Total 15) For each pair below, state whether the two compounds are enantiomers, diastereomers, conformational isomers, structure isomers or identical compounds (you may use some definitions more than once and others not at all. (12 points) a) CH Hac\%\CH8 g: (: fly ma 13:35:49 CH3 b) CH3 CH3 CH3 CH3 C) Br Br AK AF Br Br “Mums d) OH OH u-ul Extra Credit 1 (4 points) Give something you liked about the course and also something that could be improved for next semester. 12 Page Point Totael Extra Credit 2: (10 points) Given the following retrosynthetic analysis, show how to synthesize the target molecule from the two starting alcohols. ll: geé W 13 Page Point Totael Scratch Paper Only — Nothing Written on this page will be graded. periodic table of the elements icirgsfim mm “m mm“ L Inn’s yum 18 swam» 1 _ W rt ynimog max- K.) W: I :- W47?!“ '1 ‘ ' —— Barnum ‘ ' W Atomic fin»- 14 15 2 W" ' Mini-m Svmbul L) 39 Arumic x; cm Weight mm‘esxun 12 M g mg 3 4 s 6 7 ‘ ° mew «mam man-nu «mam nmmim mumesa rm ccmn mm worm am: $21 22 23 25 C27 23 23 30' wen; 1M swear I a: 7 wm .4: saw; as w; 63 548 mm mmram 1 Him [31 mm ram: m um: mlmuns x; mm zmmm mom , -' 39 fl M O .4 ‘ ml: 6, M mum" m'mmu Amway uranium Emmi mm at: 8c; #29 0:31 mum-m 19f- (ifl \ E Liquids elements riy u: Vain/nu (em—tr 4 Graven; «instants at My L3 synthcfie. «imam!» Score: 14 I’: urgua 121$" , mam: Smimetk‘afim yah’frzmm Page Point Totael ...
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